


Cross Dressing

by AeonFlux40



Series: Kinktober 2018 [11]
Category: Supernatural
Genre: Crossdressing, Dean Winchester Loves Sam Winchester, Dubious Consent, Embarrassed Sam Winchester, Implied/Referenced Underage Sex, Incest, M/M, Sibling Incest
Language: English
Status: Completed
Published: 2019-01-24
Updated: 2019-01-24
Packaged: 2019-10-15 11:41:57
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 974
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17528057
Author URL: https://archiveofourown.org/users/AeonFlux40/pseuds/AeonFlux40
Summary: Dean finds out his little brother likes to wear skirts and panties. Dean is 18, and Sam is 14.





	Cross Dressing

Dean was out at the laundromat washing clothes when he found a pair of panties mixed in with his clothes. _Hmmm. I don’t remember these. _He shrugged and tossed them in with the rest of the clothes. Further down in the duffle bag, Dean found a skirt and a pink tank top. Now he was totally confused. _What the hell? _He had no idea where these random clothes came from. Dean thought maybe his stuff got mixed up in the last laundry run, but whatever. He decided to wash them anyway.____

When Dean got to back the motel room, he found Sam rummaging around in his bag. He seemed a bit frantic, like he lost something important. A light went off in Dean’s brain. _Aha. So that’s where those clothes came from. _Dean snickered. The thought of his brother holding on to girl’s clothes amused him for some reason.__

“Something wrong, Sammy?”

“Oh! Uh, n-no. I’m good.”

“You lookin’ for these?” Dean walked over to him and pulled out the girl clothes from the duffel bag he was holding.

“Dean, where’d you get those?” Sam grabbed the clothing from his older brother, his cheeks flushed red with obvious embarrassment.

“They were in with the laundry. What the hell are you doing with these?”

“They belonged to this girl I was sort of seeing at the last place we stayed.” Sam was such a horrible liar.

“Oh, yeah? What’s her name?” Dean crossed his arms across his chest.

“Misty.” Sam refused to look at his brother. His face was getting redder by the second. He shifted from one foot to the other. Dean could tell his little brother was nervous and it turned him on a bit. He was kind of adorable when he had that lost puppy look on his face. Add a pair of dimples and innocent hazel eyes to the mix, it was a perfect trifecta.

“Uh-huh. Right. You know, I can always tell when you’re lying, Sam.”

Sam looked like he was about to cry. “Dean, please. You can’t tell dad about this, he’ll kill me!” Sam’s grip on the clothing was knuckle white. He was scared of Dean telling their dad, but more frightened of what his dad might do to him when he found out. Although their father never actually said it, the boys knew John would never approve of any kind of “alternative lifestyle”. Especially if said lifestyle could expose them in any way. “Fess up Sam. These clothes don’t belong to some random girl. They’re yours, aren’t they?”

Sam nodded. “I didn’t want to tell you because I’m embarrassed. I like wearing girl’s clothes. They’re soft and pretty and they make me feel real good. Dean, please promise me you won’t say anything to dad.”

“Put ‘em on, then.”

“What?” Sam was confused. He had no idea his brother would say that.

“You heard me. You don’t want me telling dad about these, go and put ‘em on for me. I wanna see you wearing them.”

“But you’ll laugh at me.”

“I promise not to laugh at you, Sammy.”

Sam knew Dean wasn’t kidding. He had that stern look on his face. Sam knew that if he didn’t do what Dean said, there’d be hell to pay. He loved his older brother, but sometimes he was just like their father. Sam didn’t like that at all. He felt it was best to just keep his head down and do what he was told. Sam didn’t want to dress up in front of Dean, but if that’s what it took for him to keep this secret from John, then he was all for it. He never had anything that he could call _his _except for this. Sam wasn’t ready to lose that.__

“Okay, Dean. I’ll go change.”

Sam stepped out of the bathroom and stood in front of Dean. He wasn’t ashamed for liking girl’s clothing, he just didn’t want his brother to see him wearing them. It was private, for Sam only. There were times when Dean and John would go out and leave Sam alone in the motel room. He’d put on a pair of panties and walk around with nothing else on. He was fearful that their father would find out, and he was careful to keep whatever he had stashed away. There were a few times he had to get rid of some clothes and that really hurt him. Sam watched as Dean eyed him up and down, a strange look in his eyes. It was the same look he’d give the waitresses at various diners they stopped at. He knew that look and it made him a little scared. Sam crossed his arms over his chest, the thin fabric of the tank top wasn’t doing much to keep him warm and he was sure Dean could see his nipples.

“Turn around and face the wall.”

“Why?”

“Just do it.”

Sam nodded and faced the wall. “You promised you wouldn’t laugh.”

“Oh Sammy, trust me. I’m not laughing.” Sam heard Dean rustling around a bit. He was curious about what Dean was doing but didn’t dare look. There were footsteps behind him and suddenly Dean was right up against him.

“You wanna dress like a bitch, I’m gonna fuck you like one.” Dean growled in Sam’s ear. He reached up under the skirt and grabbed Sam’s ass, making him gasp. “Mmmm, Sammy. I’ve been thinking about doing this for a while.” Deans hands roamed around to the front and grabbed Sam’s dick. “You’ve gotten big, baby brother.” Sam whimpered and pushed back against Dean.

“Dean, please. I don’t think we should be doing this.”

“I don’t really care what you think.” Dean bit down on the nape of Sam’s neck. “Gonna mark you up and make you mine tonight. My little brother. My Sammy.”

**Author's Note:**

> This took a different turn than I had originally imagined. It was just going to be Dean telling Sam that everything was okay, he wasn’t going to rat on him, etc. Then I remembered that I’m writing for Kinktober and decided to change it up a bit. I hope y’all like it.


End file.
